Compound including indole derivative in which two tertiary amines are substituted, organic electronic element using same, and terminal thereof

ABSTRACT

Disclosed are a compound including an indole derivative in which two tertiary amines are substituted, an organic electronic element using the same, and a terminal thereof.

TECHNICAL FIELD

The present invention relates to a compound including an indolederivative in which two tertiary amines are substituted, an organicelectronic element using the same, and a terminal thereof.

BACKGROUND ART

In general, an organic light emitting phenomenon indicates conversion ofelectric energy into light energy by means of an organic material. Anorganic electronic element using the organic light emitting phenomenongenerally has a structure including an anode, a cathode, and an organicmaterial layer interposed therebetween. Herein, in many cases, theorganic material layer may have a multi-layered structure havingrespective different materials in order to improve efficiency andstability of an organic electronic element. For example, it may includea hole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer, and the like.

Materials used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, etc. according to their functions. Then, the lightemitting material may be divided into a high molecular weight type and alow molecular weight type according to their molecular weight, and maybe divided into a fluorescent material from electronic singlet excitedstates and a phosphorescent material from electronic triplet excitedstates according to their light emitting mechanism. Further, the lightemitting material can be classified into a blue, green or red lightemitting material and a yellow or orange light emitting materialrequired for giving a more natural color, according to a light emittingcolor.

Meanwhile, when only one material is used as a light emitting material,an efficiency of a device is lowered owing to a maximum luminescencewavelength being shifted to a longer wavelength due to the interactionbetween the molecules, the deterioration of color purity and thereduction in luminous efficiency. Therefore, a host/dopant system can beused as the light emitting material for the purpose of enhancing thecolor purity and the luminous efficiency through energy transfer. It isbased on the principle that if a small amount of a dopant having asmaller energy band gap than a host forming an emitting layer is mixedwith the emitting layer, excitons which are generated in the emittinglayer are transported to the dopant, thus emitting a light having a highefficiency. Here, since the wavelength of the host is shifted accordingto the wavelength of the dopant, a light having a desired wavelength canbe obtained according the kind of the dopant.

In order to allow the organic electronic element to fully exhibit theabove-mentioned excellent characteristics, a material constituting theorganic material layer in the device, for example, a hole injectionmaterial, a hole transport material, a light emitting material, anelectron transport material and an electron injection material should beessentially composed of a stable and efficient material. However, thedevelopment of a stable and efficient organic material layer materialfor the organic electronic element has not yet been fully realized.Accordingly, the development of new materials is continuously desired.

DETAILED DESCRIPTION OF THE INVENTION Technical Problem

In order to solve the above-mentioned problems occurring in the priorart, through embodiments of the present invention, a compound includingan indole derivative in which two tertiary amines are substituted wasfound. Further, it was found that when applied in an organic electronicelement, the compound can highly improve luminous efficiency, stability,and life span of the device.

Accordingly, an object of the present invention is to provide a compoundincluding an indole derivative in which two tertiary amines aresubstituted, an organic electronic element using the same, and aterminal thereof.

Technical Solution

In accordance with an aspect of the present invention, there is provideda compound represented by Formula below.

The inventive compound including an indole derivative in which twotertiary amines are substituted may be used as a material for holeinjection, hole transport, electron injection, electron transport, lightemission, and/or passivation (capping), and especially, may be usedalone as a light emitting material, a host, a dopant, a hole injectionlayer or a hole transport layer.

Also, the present invention provides an organic electronic element usingthe compound having Formula above, and an electronic device or aterminal which includes the organic electronic element.

Advantageous Effects

The inventive compound including an indole derivative in which twotertiary amines are substituted may perform various roles in an organicelectronic element and a terminal. Also, when the compound is applied tothe organic electronic element or the terminal, it is possible to reducea driving voltage of the element, and improve luminous efficiency, lifespan, and stability of the device.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1 to 6 show examples of an organic electro-luminescence elementwhich can employ a compound according to the present invention.

MODE FOR CARRYING OUT THE INVENTION

Hereinafter, exemplary embodiments of the present invention will bedescribed in detail with reference to the accompanying drawings. Indesignation of reference numerals to components in respective drawings,it should be noted that the same elements will be designated by the samereference numerals although they are shown in different drawings.Further, in the following description of the present invention, adetailed description of known functions and configurations incorporatedherein will be omitted when it may make the subject matter of thepresent invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

The present invention provides a compound represented by Formula 1below.

(1) R1 to R3 may be the same or different, and each may independentlyrepresent: a C₆˜C₆₀ aryl group unsubstituted or substituted with atleast one selected from the group including hydrogen, a halogen group, aC₁˜C₆₀ alkyl group, a C₁˜C₆₀ alkoxy group, a C₁˜C₆₀ alkylamine group, aC₁˜C₆₀ arylamine group, a C₁˜C₆₀ alkyl thiophene group, a C₆˜C₆₀ arylthiophene group, a C₂˜C₆₀ alkenyl group, a C₂˜C₆₀ alkynyl group, aC₃˜C₆₀ cycloalkyl group, a C₆˜C₆₀ aryl group, a C₆˜C₆₀ aryl groupsubstituted with deuterium, a C₈˜C₆₀ arylalkenyl group, a substituted orunsubstituted silane group, a substituted or unsubstituted boron group,a substituted or unsubstituted germanium group, and a substituted orunsubstituted C₅˜C₆₀ heterocyclic group; a C₅˜C₆₀ heterocyclic groupunsubstituted or substituted with at least one selected from the groupincluding halogen, CN, NO₂, a C₁˜C₆₀ alkyl group, a C₁˜C₆₀ alkoxy group,a C₁˜C₆₀ alkylamine group, a C₁˜C₆₀ arylamine group, a C₁˜C₆₀ alkylthiogroup, a C₂˜C₆₀ alkenyl group, a C₂˜C₆₀ alkynyl group, a C₃˜C₆₀cycloalkyl group, a C₆˜C₆₀ aryl group, a C₆˜C₆₀ aryl group substitutedwith deuterium, a substituted or unsubstituted silane group, asubstituted or unsubstituted boron group, a substituted or unsubstitutedgermanium group, and a substituted or unsubstituted C₅˜C₆₀ heterocyclicgroup; or a fused cyclic group of a C₆˜C₆₀ aromatic ring with a C₄˜C₆₀aliphatic ring, or any group selected from the group consisting of ahydrogen atom, a halogen atom, a substituted or unsubstituted aliphatichydrocarbon group, a substituted or unsubstituted aryl group, and asubstituted or unsubstituted C₅˜C₆₀ hetero aryl group including at leastone of sulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon(Si).

(2) an indole derivative may have two or more diarylamine groups.

(3) n represents 1 to 3.

(4) X may be the same as R1 to R3, wherein X may form a saturated orunsaturated ring together with an adjacent group. For example, X mayform a saturated or unsaturated ring together with at least one adjacentR1 to R3. m of X is 3 or more.

(5) Ar1 to Ar5 may be the same or different, and each may beindependently a substituted or unsubstituted C₁˜C₆₀ aryl or hetero arylgroup, and Ar2 to Ar5 each may be a substituted or unsubstituted alkylgroup.

(6) L may represent a substituted or unsubstituted arylene group, asubstituted or unsubstituted hetero arylene group, a divalent ortrivalent group selected from the group including, substituted orunsubstituted aliphatic hydrocarbons, or a divalent linking group.

The compound having the above described structural formula may be usedin a soluble process. In other words, through the soluble process, thecompound may be used for forming an organic material layer of an organicelectronic element that will be described later. In other words, theorganic material layer of the organic electronic element may bemanufactured with a smaller number of layers by using various polymermaterials by means of a solvent process (e.g., spin coating, dipcoating, doctor blading, screen printing, inkjet printing, or thermaltransfer) instead of deposition.

In the Formula 1 above, in the case of Ar2=Ar3=Ar4=Ar=5, the compoundmay be represented by Formula 2 below.

Meanwhile, in the Formula 1 above, in the case of Ar2=Ar4, Ar3=Ar5,Ar2≠Ar3, and Ar4≠Ar5 ((Ar2≠Ar3)=(Ar4≠Ar5)), the compound may berepresented by Formula 3 below.

in Formulas 1 to 3 above, substituents of R1 to R3, X, and Ar1 to Ar5may be substituted or unsubstituted. When substituted, they each may beindependently substituted with: a C₆˜C₆₀ aryl group unsubstituted orsubstituted with at least one selected from the group includinghydrogen, a halogen group, a C₁˜C₆₀ alkyl group, a C₁˜C₆₀ alkoxy group,a C₁˜C₆₀ alkylamine group, a C₁˜C₆₀ arylamine group, a C₁˜C₆₀ alkylthiophene group, a C₆˜C₆₀ aryl thiophene group, a C₂˜C₆₀ alkenyl group,a C₂˜C₆₀ alkynyl group, a C₃˜C₆₀ cycloalkyl group, a C₆˜C₆₀ aryl group,a C₆˜C₆₀ aryl group substituted with deuterium, a C₈˜C₆₀ arylalkenylgroup, a substituted or unsubstituted silane group, a substituted orunsubstituted boron group, a substituted or unsubstituted germaniumgroup, and a substituted or unsubstituted C₅˜C₆₀ heterocyclic group; aC₅˜C₆₀ heterocyclic group unsubstituted or substituted with at least oneselected from the group including halogen, CN, NO₂, a C₁˜C₆₀ alkylgroup, a C₁˜C₆₀ alkoxy group, a C₁˜C₆₀ alkylamine group, a C₁˜C₆₀arylamine group, a C₁˜C₆₀ alkylthio group, a C₂˜C₆₀ alkenyl group, aC₂˜C₆₀ alkynyl group, a C₃˜C₆₀ cycloalkyl group, a C₆˜C₆₀ aryl group, aC₆˜C₆₀ aryl group substituted with deuterium, a substituted orunsubstituted silane group, a substituted or unsubstituted boron group,a substituted or unsubstituted germanium group, and a substituted orunsubstituted C₅˜C₆₀ heterocyclic group; or a fused cyclic group of aC₆˜C₆₀ aromatic ring with a C₄˜C₆₀ aliphatic ring, or any group selectedfrom the group consisting of a hydrogen atom, a halogen atom, asubstituted or unsubstituted aliphatic hydrocarbon group, a substitutedor unsubstituted aryl group, and a substituted or unsubstituted C₅˜C₆₀hetero aryl group including at least one of sulfur (S), nitrogen (N),oxygen (O), phosphorous (P) and silicon (Si).

Specific examples of a compound including an indole derivative accordingto one embodiment of the present invention, represented by Formulas 1 to3, may include compounds represented by Formula 4 below. However, thepresent invention is not limited thereto. In other words, herein, sincein the compounds represented by Formulas 1 to 3, there are wide range ofsubstituted or unsubstituted substituents for substituents of R1 to R3,X, and Ar1 to Ar5, it is practically difficult to exemplify all ofcompounds. Thus, although representative compounds are illustrativelydescribed, this specification may cover other compounds represented byFormulas 1 to 3 not described in Formula 4.

There are various organic electronic elements employing the compoundsincluding the indole derivative, as described with reference to Formulas1 to 4, as organic material layers. The organic electronic element inwhich the compounds including the indole derivative, as described withreference to Formulas 1 to 4, can be employed may include, for example,an organic light emitting diode (OLED), an organic solar cell, anorganic photo conductor (OPC) drum, an organic transistor (organic TFT),and the like.

As one example of the organic electronic elements in which compoundsincluding the indole derivative, as described with reference to Formulas1 to 4, can be used, an organic light-emitting diode (OLED) will bedescribed below, but the present invention is not limited thereto. Theabove described compounds may be applied to various organic electronicelements.

In another embodiment of the present invention, there is provided anorganic electro-luminescence element as an organic electronic elementincluding a first electrode, a second electrode, and an organic materiallayer interposed between these electrodes, in which at least one oforganic material layers includes the compounds represented by Formulas 1to 4.

FIGS. 1 to 6 show examples of an organic electro-luminescence elementwhich can employ a compound according to the present invention.

The organic electro-luminescence element according to another embodimentof the present invention may be manufactured by means of a manufacturingmethod and materials conventionally known in the art in such a mannerthat it can have a conventionally known structure, except that at leastone of organic material layers including a hole injection layer, a holetransport layer, an emitting layer, an electron transport layer, and anelectron injection layer is formed in such a manner that it can includethe compounds represented by Formulas 1 to 4.

The structures of the organic electro-luminescence element according toanother embodiment of the present invention are shown in FIGS. 1 to 6,but the present invention is not limited to the structures. Herein, thereference numeral 101 indicates a substrate, 102 indicates an anode, 103indicates a hole injection layer (HIL), 104 indicates a hole transportlayer (HTL), 105 indicates an emitting layer (EML), 106 indicates anelectron injection layer (EIL), 107 indicates an electron transportlayer (ETL), and 108 indicates a cathode. Although not shown, in such anorganic electro-luminescence element, a hole blocking layer (HBL) forblocking movement of holes, an electron blocking layer (EBL) forblocking movement of electrons, an emission assisting layer forsupporting or assisting light emission, and a protective layer may befurther positioned. The protective layer may be formed in such a mannerthat it, as an uppermost layer, can protect an organic material layer ora cathode.

Herein, the compound including the indole derivative, as described withreference to Formulas 1 to 4, may be included in at least one of organicmaterial layers including a hole injection layer, a hole transportlayer, an emitting layer, and an electron transport layer. Specifically,the compound including the indole derivative, as described withreference to Formulas 1 to 4, may be substituted for at least one of ahole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer, a hole blockinglayer, an electron blocking layer, an emission assisting layer, and aprotective layer, or may be used in combination with these layers so asto form layers. Of course, the compound may be used for not only onelayer of the organic material layers but also two or more layers.

Especially, the compound including the indole derivative, as describedwith reference to Formulas 1 to 4, may be used as a material for holeinjection, hole transport, electron injection, electron transport, lightemission, and passivation (capping). Especially, it may be used alone asa light emitting material, a host or a dopant.

For example, in manufacturing of the organic electro-luminescenceelement according to another embodiment of the present invention, ametal, a conductive metal oxide, or an alloy thereof may be deposited ona substrate by means of PVD (physical vapor deposition) such assputtering or e-beam evaporation, so as to form an anode, and then anorganic material layer including a hole injection layer, a holetransport layer, an emitting layer, an electron transport layer, and anelectron injection layer may be formed thereon, and a material capableof being used as a cathode may be deposited thereon.

Besides the above described method, on a substrate, a cathode material,an organic material layer, and an anode material may be sequentiallydeposited so as to provide an organic electronic element. The organicmaterial layer may be formed in a multi-layered structure including ahole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, and an electron injection layer, but thepresent invention is not limited thereto. It may be formed in a singlelayer structure. Further, the organic material layer may be manufacturedwith a smaller number of layers by using various polymer materials bymeans of a solvent process (e.g., spin coating, dip coating, doctorblading, screen printing, inkjet printing, or thermal transfer) insteadof deposition.

In the organic electro-luminescence element according to anotherembodiment of the present invention, the above described compoundincluding the indole derivative may be used in a soluble process such asa spin coating process or an ink jet process.

The substrate is a support for the organic electro-luminescence element,and may employ a silicon wafer, a quartz or glass plate, a metal plate,a plastic film or sheet.

On the substrate, an anode is positioned. Such an anode allows holes tobe injected into a hole injection layer positioned thereon. As an anodematerial, a material having a high work function is preferably used sothat injection of holes into an organic material layer can be smoothlycarried out. Specific examples of an anode material that may be used inthe present invention may include: metals (such as vanadium, chromium,copper, zinc, gold) or alloys thereof; metal oxides such as zinc oxide,indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ametal-oxide combination such as ZnO:Al or SnO₂:Sb; and conductivepolymers such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole andpolyaniline, but the present invention is not limited thereto.

On the anode, a hole injection layer is positioned. A material for sucha hole injection layer is required to have a high efficiency forinjecting holes from an anode, and to be able to efficiently transportthe injected holes. For this, the material has to have a low ionizationpotential, a high transparency in visible rays, and a high stability forholes.

As a hole injection material, a material into which holes can beefficiently injected from an anode at a low voltage is used. HOMO(highest occupied molecular orbital) of the hole injection materialpreferably ranges from a work function of an anode material to HOMO ofadjacent organic material layers. Specific examples of the holeinjection material may include metal porphyrine-, oligothiophene-, andarylamine-based organic materials, hexanitrile hexaazatriphenylene- andquinacridone-based organic materials, perylene-based organic materials,and anthraquinone-, polyaniline-, and polythiophene-based conductivepolymers, but the present invention is not limited thereto.

On the hole injection layer, a hole transport layer is positioned. Sucha hole transport layer receives holes transferred from the holeinjection layer and transfers them to an organic emitting layerpositioned thereon. Further, the hole transport layer has a high holemobility and a high hole stability and performs a role of blockingelectrons. Besides these general requirements, it requiresheat-resistance for a device when applied for an automobile display, andthus is preferably made of a material having a glass transitiontemperature (Tg) of 70° C. or more. The examples of a materialsatisfying these conditions may include NPD (or NPB),spiro-arylamine-based compound, perylene-arylamine-based compound,azacycloheptatriene compound, bis(diphenylvinylphenyl)anthracene,silicongermaniumoxide compound, silicon-based arylamine compound, andthe like.

On the hole transport layer, an organic emitting layer is positioned.Such an organic emitting layer is made of a material having a highquantum efficiency, in which holes and electrons which are injected froman anode and a cathode, respectively, are recombined so as to emitlight. As a light emitting material, a material allowing holes andelectrons transferred from a hole transport layer and an electrontransport layer, respectively, to be combined so as to emit light in avisible ray range is used. Preferably, a material having a high quantumefficiency for fluorescence or phosphorescence may be used.

As a material or a compound satisfying these conditions, for a greencolor, Alq3 may be used, and for a blue color, Balq(8-hydroxyquinolineberyllium salt), DPVBi(4,4′-bis(2,2-diphenylethenyl)-1,1′-biphenyl)based material, Spiro material,spiro-DPVBi(Spiro-4,4′-bis(2,2-diphenylethenyl)-1,1′-biphenyl),LiPBO(2-(2-benzoxazoyl)-phenol lithium salt),bis(diphenylvinylphenylvinyl)benzene, aluminum-quinoline metal complex,imidazole, thiazol and oxazole-metal complex, or the like may be used.In order to improve the luminous efficiency of a blue color, perylene,andBczVBi(3,3′[(1,1′-biphenyl)-4,4′-diyldi-2,1-ethenediyl]bis(9-ethyl)-9H-carbazole;DSA(distrylamine)) may be doped in a small amount. For a red color, agreen light emitting material may be doped with a material such asDCJTB([2-(1,1-dimethylethyl)-6-[2-(2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H-benzo(ij)quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene]-propanedinitrile)in a small amount. When a process such as inkjet printing, roll coating,spin coating, is used to form an emitting layer, a polymer such aspolyphenylenevinylene (PPV)-based polymer or poly fluorene may be usedfor an organic emitting layer.

On the organic emitting layer, an electron transport layer ispositioned. Such an electron transport layer requires a material whichhas a high efficiency for electrons injected from a cathode positionedthereon, and can efficiently transport the injected electrons. For this,a material having a high electron affinity, a high electron mobility,and a high electron stability is required. Specific examples of anelectron transport material satisfying these conditions may include Alcomplex of 8-hydroxyquinoline; complex including Alq₃; organic radicalcompound; and hydroxyflavone-metal complex, but the present invention isnot limited thereto.

On the electron transport layer, an electron injection layer is layered.

The electron injection layer may be manufactured by using a metalcomplex compound (such as Balq, Alq3, Be(bq)2, Zn(BTZ)2, Zn(phq)2, PBD,spiro-PBD, TPBI, and Tf-6P) or a low molecular material including anaromatic compound having an imidazole ring or a boron compound. Herein,the electron injection layer may be formed in a thickness range of 100 Åto 300 Å.

On the electron injection layer, a cathode is positioned. Such a cathodeperforms a role of injecting electrons. As a material for the cathode,the same material as that used for an anode may be used. In order toachieve efficient electron injection, a metal having a low work functionis more preferably used. Especially, metals such as tin, magnesium,indium, calcium, sodium, lithium, aluminum, silver, or alloys thereofmay be used. Further, a double-layered electrode (e.g., lithium fluorideand aluminum, lithium oxide and aluminum, and strontium oxide andaluminum) with a thickness of 100 μm or less may be used.

As described above, the compound including the indole derivative, asdescribed with reference to Formulas 1 to 4, may be used as a holeinjection material, a hole transport material, a light emittingmaterial, an electron transport material and an electron injectionmaterial, which are appropriate for fluorescent and phosphorescentelements of all colors (such as red, green, blue, white). Also, thecompound may be used as a material of a host (or a dopant) of variouscolors.

The organic electro-luminescence element according to the presentinvention may be manufactured in a front luminescent type, a rearluminescent type, or a both-side luminescent type according to itsmaterials.

Meanwhile, the present invention provides a terminal which includes adisplay device and a control part for driving the display device, thedisplay device including the above described organic electronic element.The terminal means a wired/wireless communication terminal which iscurrently used or will be used in the future. The above describedterminal according to the present invention may be a mobilecommunication terminal such as a cellular phone, and may include allkinds of terminals such as a PDA, an electronic dictionary, a PMP, aremote control, a navigation unit, a game player, various kinds of TVs,and various kinds of computers.

Example

Hereinafter, the present invention will be described more specificallywith reference to Preparation Examples and Test Examples. However, thefollowing examples are only for illustrative purposes and are notintended to limit the scope of the invention.

Preparation Example

Hereinafter, Preparation Examples or Synthesis Examples of the compoundsincluding the indole derivative, included in Formula 4, will bedescribed. However, since there are many compounds including the indolederivative, included in Formula 4, only one compound or two compoundsfrom among the compounds will be exemplified.

A person skilled in the art of the invention should realize that othercompounds including the indole derivative in which two tertiary aminesare substituted can be prepared through Preparation Examples asdescribed below although they are not exemplified.

Step 1) Synthesis Method of Compound A-1

1-phenyl-1H-indol-5-ylboronic acid,4′-bromo-N3,N3,N5,N5-tetraphenylbiphenyl-3,5-diamine, and Pd(PPh₃)₄ weredissolved in THF 500 ml, and 250 ml of water, and K₂CO₃ was addedthereto. The resultant solution was heated under reflux for 24 hours.The obtained solid was washed with water and methanol, and purified bysilica gel column chromatography to give a white solid, compound A-1(yield: 62%).

Step 2) Synthesis Method of Compound B-7

Compound B-7 was synthesized in the same manner as described in thesynthesis method of compound A-1 except that instead of4′-bromo-N3,N3,N5,N5-tetraphenylbiphenyl-3,5-diamine,N1,N3-di(biphenyl-4-yl)-5-bromo-N1,N3-bis(9,9-dimethyl-9H-fluoren-2-yl)benzene-1,3-diaminewas used (synthesis yield: 70%).

Also, compounds A-7 and B-9 were synthesized in the same or similarmanner as described in the synthesis methods of compounds A-1 and B-7.

Herein, in the compounds represented by Formulas 1 to 3, since there arewide range of substituted or unsubstituted substituents for substituentsof R1 to R3, X, and Ar1 to Ar5, Synthesis Examples of only a part ofcompounds represented by Formula 4 have been illustratively described.However, this specification may cover other compounds represented byFormulas 1 to 4 whose Synthesis Examples have been not illustrativelydescribed.

Fabrication Test of Organic Electro-Luminescence Device

An organic electro-luminescence element was manufactured through aconventional method by using the synthesized various compounds as alight emitting host material of an emitting layer or as a hole transportlayer. First, on an ITO layer (anode) formed on a glass substrate, a4,4′,4″-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (hereinafter,referred to as 2T-NATA) film as a hole injection layer wasvacuum-deposited with a thickness of 10 nm.

Then, the developed material as a hole transport compound wasvacuum-deposited with a thickness of 30 nm so as to form a holetransport layer. After the hole transport layer was formed, for themeasurement on the developed material as the hole transport layer, onthe hole transport layer, an emitting layer doped with 7% BD-052X(Idemitus) with a thickness of 45 nm was applied (herein, BD-052X was ablue fluorescent dopant, and an emitting host material was9,10-di(naphthalene-2-anthracene (AND)).

As a hole blocking layer,(1,1-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, referred to as BAlq) was vacuum-deposited with a thicknessof 10 nm, and then as an electron injection layer,tris(8-quinolinol)aluminum (hereinafter, referred to as Alq₃) wasfilm-formed with a thickness of 40 nm. Then, LiF (alkali-metal halide)was deposited with a thickness of 0.2 nm, and Al was deposited with athickness of 150 nm. The Al/LiF was used as a cathode while the organicelectro-luminescence device was fabricated.

Comparison Test Example

In order to compare to the case where the inventive compounds were usedas hole transport layers, instead of the inventive compound, thecompound represented by Formula 5 below (hereinafter, referred to asNPD) was used as a hole transport material so as to fabricate an organicelectro-luminescence device with the same structure as that of TestExample.

TABLE 1 hole current luminous chromaticity transport voltage densityefficiency coordinates material (V) (mA/cm²) (cd/A) (x, y) Example 1compound 6.3 12.44 9.7 (0.15, 0.13) A-1 Example 2 compound 6.2 12.35 9.3(0.15, 0.15) A-7 Example 3 compound 5.7 12.77 10.0 (0.15, 0.12) B-7Example 4 compound 5.6 12.69 9.9 (0.15, 0.14) B-9 Comparative NPB 7.213.35 7.5 (0.15, 0.15) Example 1

From the results noted in Table 1, it can be seen that in an organicelectro-luminescence device using the inventive material for the organicelectro-luminescence device, it is possible to obtain long-life bluelight with a high efficiency, and an improved color purity. Thus, theinventive material as a hole transport material for an organicelectro-luminescence device can lower a driving voltage, andsignificantly improve the luminous efficiency and life span.

It is natural that even though the inventive compounds are employed inother organic material layers of an organic electro-luminescenceelement, e.g., an emitting layer, an emission assisting layer, anelectron injection layer, an electron transport layer and a holeinjection layer as well as a hole transport layer, it is possible toachieve the same effects.

Herein, in the compounds represented by Formulas 1 to 4, since there area wide range of substituted or unsubstituted substituents of R1 to R3,X, and Ar1 to Ar5, Comparative Examples of only a part of compoundsrepresented by Formula 4 have been illustratively described. However, itcan be found that compounds whose Comparative Examples represented byFormulas 1 to 3 have been not illustratively described show the sameeffect as the above described Comparative Examples because they have ascaffold of Formulas 1 to 3 as described above. Thus, this specificationmay cover the results.

In the above, although the embodiments of the present invention havebeen described with reference to the accompanying drawings, a personskilled in the art should apprehend that the technical configuration ofthe present invention can be embodied in other specific forms withoutdeparting from the technical spirit or essential characteristicsthereof. Thus, the embodiments described above should be construed asexemplary in every aspect and not limiting. Furthermore, the scope ofthe present invention is defined by the appended claims rather than theabove detailed description. Thus, the present invention should beconstrued to cover all modifications or variations induced from themeaning and range of the appended claims and their equivalents.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority from and the benefit under 35 U.S.C.§119(a) of Korean Patent Application No. 10-2010-0022304, filed on Mar.12, 2010, which is hereby incorporated by reference for all purposes asif fully set forth herein. Further, this application claims the benefitof priority in other countries than U.S., which are hereby incorporatedby reference herein.

1. A compound represented by Formula below,

(1) R1 to R3, and X are the same or different, and each independentlyrepresents: a C₆˜C₆₀ aryl group unsubstituted or substituted with atleast one selected from the group including hydrogen, a halogen group, aC₁˜C₆₀ alkyl group, a C₁˜C₆₀ alkoxy group, a C₁˜C₆₀ alkylamine group, aC₁˜C₆₀ arylamine group, a C₁˜C₆₀ alkyl thiophene group, a C₆˜C₆₀ arylthiophene group, a C₂˜C₆₀ alkenyl group, a C₂˜C₆₀ alkynyl group, aC₃˜C₆₀ cycloalkyl group, a C₆˜C₆₀ aryl group, a C₆˜C₆₀ aryl groupsubstituted with deuterium, a C₈˜C₆₀ arylalkenyl group, a substituted orunsubstituted silane group, a substituted or unsubstituted boron group,a substituted or unsubstituted germanium group, and a substituted orunsubstituted C₅˜C₆₀ heterocyclic group; a C₅˜C₆₀ heterocyclic groupunsubstituted or substituted with at least one selected from the groupincluding halogen, CN, NO₂, a C₁˜C₆₀ alkyl group, a C₁˜C₆₀ alkoxy group,a C₁˜C₆₀ alkylamine group, a C₁˜C₆₀ arylamine group, a C₁˜C₆₀ alkylthiogroup, a C₂˜C₆₀ alkenyl group, a C₂˜C₆₀ alkynyl group, a C₃˜C₆₀cycloalkyl group, a C₆˜C₆₀ aryl group, a C₆˜C₆₀ aryl group substitutedwith deuterium, a substituted or unsubstituted silane group, asubstituted or unsubstituted boron group, a substituted or unsubstitutedgermanium group, and a substituted or unsubstituted C₅˜C₆₀ heterocyclicgroup; or a fused cyclic group of a C₆˜C₆₀ aromatic ring with a C₄˜C₆₀aliphatic ring, or any group selected from the group consisting of ahydrogen atom, a halogen atom, a substituted or unsubstituted aliphatichydrocarbon group, a substituted or unsubstituted aryl group, and asubstituted or unsubstituted hetero aryl group including at least one ofsulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si);(2) an indole derivative has two or more diarylamine groups; (3) nrepresents 1 to 3; (4) m of X is 3 or more; (5) Ar1 to Ar5 are the sameor different, and each is independently a substituted or unsubstitutedC₁˜C₆₀ aryl or hetero aryl group.
 2. The compound as claimed in claim 1,wherein Ar2=Ar3=Ar4=Ar5.
 3. The compound as claimed in claim 1, whereinAr2=Ar4, Ar3=Ar5, Ar2≠Ar3, and Ar4≠Ar5.
 4. The compound as claimed inclaim 1, wherein R1 to R3, and X form a saturated or unsaturated ringtogether with an adjacent group.
 5. The compound as claimed in claim 1,wherein the compound is at least one of compounds below.


6. An organic electronic element comprising one or more organic materiallayers comprising the compound as claimed in any one of claims 1 to 5.7. The organic electronic element as claimed in claim 6, wherein theorganic material layers are formed by a soluble process of the compound.8. The organic electronic element as claimed in claim 6, wherein theorganic electronic element is an organic electro-luminescence element inwhich a first electrode, said one or more organic material layers, and asecond electrode are sequentially layered.
 9. The organic electronicelement as claimed in claim 8, wherein the organic material layerscomprise any one of a hole injection layer, a hole transport layer, anemitting layer, an electron transport layer, and an electron injectionlayer.
 10. The organic electronic element as claimed in claim 8, whereinthe organic material layers comprise a hole injection layer, and thehole injection layer comprises the compound.
 11. A terminal comprising adisplay device and a control part for driving the display device, thedisplay device comprising the organic electronic element as claimed inclaim
 8. 12. The terminal as claimed in claim 11, wherein the organicelectronic element is any one of an organic light emitting diode (OLED),an organic solar cell, an organic photo conductor (OPC) drum, and anorganic transistor (organic TFT).